Solid-phase synthesis of benzimidazole libraries biased for RNA targets

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2807-2811

  Vourloumis, Dionisios ^a   Takahashi, Masayuki ^a   Simonsen, Klaus B ^a   Ayida, Benjamin K ^a   Barluenga, Sofia ^a   Winters, Geoffrey C ^a   Hermann, Thomas ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Benzimidazoles; NMR quantitation; Privileged structures; RNA targets

Indexed keywords

ASTEMIZOLE; BENZIMIDAZOLE; OMEPRAZOLE; RNA;

ARTICLE; BIOLOGICAL MONITORING; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RNA BINDING; SOLID; STANDARD;

EID: 0037474661     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00453-2     Document Type: Article

References (44)

1. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
2. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
3. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
4. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
5. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
6. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
7. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
8. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
9. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
10. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
11. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
12. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
13. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
14. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
15. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
16. For previously published synthesis of benzimidazole-based libraries, see: (a) Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 28, 4887-4890; (b) Sun, Q.; Yan, B. Bioorg. Med. Chem. Lett. 1998, 8, 361-364; (c) Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201-204; (d) Wei, G. P.; Phillips, G. B. Tetrahedron Lett. 1998, 39, 179-182; (e) Thomas, J. B.; Fall, M. J.; Cooper, J. B.; Burgess, J. P.; Carroll, F. I. Tetrahedron Lett. 1997, 38, 5099-5102; (f) Huang, W.; Scarborough, R. M. Tetrahedron Lett. 1999, 40, 2665-2668; (g) Smith, J. M.; Gard, J.; Cummings, W.; Kanizasi, A.; Krchňák, V. J. Comb. Chem. 1999, 1, 368-370; (h) Yeh, C.; Sun, C. Synlett 1999, 6, 810-812; (i) Mayer, J. P.; Lewis, G. S.; McGee, C.; Bankaitis-Davis, D. Tetrahedron Lett. 1998, 39, 6655-6658; (j) Tumelty, D.; Schwarz, K.; Needels, M. C. Tetrahedron Lett. 1998, 39, 7467-7470; (k) Tumelty, D.; Schwarz, K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185-6188; (l) Kilburn, J. P.; Lau, J.; Jones, R. C. F. Tetrahedron Lett. 2000, 41, 5419-5421; (m) Smith, J. M.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636; (n) Farrant, E.; Rahman, S. S. Tetrahedron Lett. 2000, 41, 5383-5386; (o) Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M.; Shaw, K. J. Bioorg. Med. Chem. Lett. 2000, 10, 963-966; (p) Yeh, C.; Tung, C.; Sun, C. J. Comb. Chem. 2000, 2, 341-348.
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